Scandium-Catalyzed Electrochemical Synthesis of α-Pyridinyl Tertiary Amino Acids and Esters.

Org Lett

Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, National Demonstration Center for Experimental Chemistry Education, Nanjing University, Nanjing 210023, China.

Published: October 2023

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α-Pyridyl tertiary amino acids have potential pharmaceutical applications because of their structural features. However, their synthesis is still highly limited. Herein, we report a straightforward approach for the electrochemical synthesis of tertiary α-substituted amino acid derivatives via three-component reductive coupling. Using gaseous ammonia as both the N and H source, the α-keto ester reacts directly with 4-CN-pyridine. The application of scandium catalysis is the key for achieving chemoselectivity among various side reaction pathways.

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http://dx.doi.org/10.1021/acs.orglett.3c02734DOI Listing

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